Don Draper (Jon Hamm)

Don spends most of season 5 hurling himself into his marriage to Megan, unconcerned with how his job is suffering in the process. When Megan quits the agency to pursue an acting career, Don is set adrift, but eventually dives back into SCDP to land the Jaguar campaign — which he can't even enjoy because he knows Joan prostituted herself to help land the account. After helping Megan get her big break in a commercial, Don feels disconnected from work and home, and goes alone to a bar like he did in the old days. When last we see him, an attractive woman is hitting on him on behalf of her friend, asking, "Are you alone?" We'll find out the answer in season 6.